Hydrogenation of Esters

Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries

Volumn , Issue , 2013, Pages 37-61

  Saudan, Lionel A ^a  

^a Analysis and Perception Department   (Switzerland)

Author keywords

Agrochemical industry; Aliphatic esters; Aromatic esters; Catalytic hydrogenation; Chiral esters; Furanoic esters; Lactones; pharmaceutical industry

Indexed keywords

EID: 84886215320     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118354520.ch02     Document Type: Chapter

References (102)

1. For reviews on the chemistry of odorants, see (a) Mimoun H (1996). Catalytic opportunities in the flavor and fragrance industry. Chimia 50, 620-625.
2. Fráter G, Bajgrowicz JA, Kraft P (1998). Fragrance chemistry. Tetrahedron 54, 7633-7703.
3. Yamamoto T. Advances in the transition metal (Rh, Ru)-BINAP-catalyzed asymmetric synthesis of chiral compounds for flavours and fragrances and their associated sensory properties. In: Swift KAD, editor. Current Topics in Flavour and Fragrances. Takasago Int. Co.; 1999, pp 33-58.
4. Kraft P, Bajgrowicz JA, Denis C, Fráter G (2000). Odds and trends: recent developments in the chemistry of odorants. Angew. Chem., Int. Ed. 39, 2980-3010.
5. Chapuis C, Jacoby D (2001). Catalysis in the preparation of fragrances and flavours. Appl. Catal. A: Gen. 221, 93-117.
6. Swift KAD (2004). Catalytic transformations of the major terpene feedstocks. Top. Catal. 27, 143-155.
7. Saudan LA (2007). Hydrogenation processes in the synthesis of perfumery ingredients. Acc. Chem. Res. 40, 1309-1319.
8. Birkbeck AA. Challenges in the synthesis of natural and non-natural volatiles. In: Herrmann A, editor. The Chemistry and Biology of Volatiles. Wiley, Chichester; 2010, pp 173-202.
9. Adkins H, Folkers K (1931). The catalytic hydrogenation of esters to alcohols. J. Am. Chem. Soc. 53, 1095-1097.
10. Pouilloux Y, Autin F, Barrault J (2000). Selective hydrogenation of methyl oleate into unsaturated alcohols. Relationships between catalytic properties and composition of cobalt-tin catalysts. Catal. Today 63, 87-100 and references therein.
11. Weissermel K, Arpe HJ. Industrial Organic Chemistry. VCH Publishers, New York; 1993.
12. Ho LTT. Formulating Detergents and Personal Care Products. AOCS Press, New York; 2000.
13. Hayes DG. Biobased surfactants: Overview and industrial state of the art. In: Hayes DG, Kitamoto D, Solaiman DKY, Ashby RD, editors. Biobased Surfactants and Detergents. AOCS Press, Urbana; 2009, pp 3-25.
14. Minnaard AJ, Feringa BL, Lefort L, De Vries JG (2007). Asymmetric hydrogenation using monodentate phosphoramidite ligands. Acc. Chem. Res. 40, 1267-1277.
15. Roseblade SJ, Pfaltz A (2007). Iridium-catalyzed asymmetric hydrogenation of olefins. Acc. Chem. Res. 40, 1402-1411.
16. Oro LA, Carmona D. Rhodium. In: de Vries JG, Elsevier CJ, editors. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim; 2007, pp 3-30.
17. Noyori R, Ohkuma T (2001). Asymmetric catalysis by architectural and functional molecular engineering: practical chemo- and stereoselective hydrogenation of ketones. Angew. Chem., Int. Ed. 40, 40-73.
18. Ohkuma T, Noyori R. Enantioselective ketone and b-keto ester hydrogenations (including mechanisms). In: de Vries JG, Elsevier CJ, editors. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim; 2007, pp 1105-1163.
19. Blaser HU, Spindler F, Thommen M. Industrial applications. In: de Vries, JG, Elsevier CJ, editors. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim; 2007, pp 1279-1324.
20. Blaser HU, Malan C, Pugin B, Spindler F, Steiner H, Studer M (2003). Selective hydrogenation for fine chemicals: recent trends and new developments. Adv. Synth. Catal. 345, 103-151.
21. 2(diamine) precatalysts as a practical alternative to sodium borohydride for ketone reduction. Org. Process Res. Dev. 10, 1054-1058.
22. Tanielyan SK, Marin N, Alvez G, Augustine RL (2006). Two efficient enantioselective syntheses of 2-amino-1-phenylethanol. Org. Process Res. Dev. 10, 893-898.
23. Johnson NB, Lennon IC, Moran PH (2007). Industrialscale synthesis and applications of asymmetric hydrogenation catalysts. Acc. Chem. Res. 40, 1291-1299.
24. Ito M, Ikariya T (2007). Catalytic hydrogenation of polar organic functionalities based on Ru-mediated heterolytic dihydrogen cleavage. Chem. Commun. 5134-5142.
25. Tsutsumi K, Katayama K, Utsumi N, Murata K, Arai N, Kurono N, Ohkuma T (2009). Practical asymmetric hydrogenation of 3-quinuclidinone catalyzed by the XylSkewphos/ PICA-ruthenium(II) complex. Org. Process Res. Dev. 13, 625-628.
26. For a review on previous ruthenium catalyzed hydrogenation of esters, see Clarke ML, Roff GJ. Homogeneous hydrogenation of aldehydes, ketones, imines and carboxylic acid derivatives: chemoselectivity and catalytic activity. In: de Vries JG, Elsevier CJ, editors. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim; 2007, pp 413-454.
27. Teunissen HT, Elsevier CJ (1997). Ruthenium catalyzed hydrogenation of dimethyl oxalate to ethylene glycol. Chem. Commun. 667-668.
28. Teunissen HT, Elsevier CJ. (1998). Homogeneous ruthenium catalyzed hydrogenation of esters to alcohols.Chem.Commun. 1367-1368.
29. vanEngelen MC, Teunissen HT, de Vries JG, Elsevier CJ (2003). Suitable ligands for homogeneous rutheniumcatalyzed hydrogenolysis of esters. J. Mol. Catal. A: Chem. 206, 185-192.
30. For the use of other tripodal ligands in ester hydrogenation, see (a) Boardman B, Hanton MJ, van Rensburg H, Tooze RP (2006). A tripodal sulfur ligand for the selective ruthenium-catalyzed hydrogenation of dimethyl oxalate. Chem. Commun. 2289-2291.
31. Hanton MJ, Tin S, Boardman BJ, Miller P (2011). Ruthenium-catalyzed hydrogenation of esters using tripodal phosphine ligands. J. Mol. Catal. A: Chem. 346, 70-78.
32. Zhang J, Leitus G, Ben-David Y, Milstein D (2006). Efficient homogeneous catalytic hydrogenation of esters to alcohols. Angew. Chem., Int. Ed. 45, 1113-1115.
33. Milstein D (2010). Discovery of environmentally benign catalytic reactions of alcohols catalyzed by pyridine-based pincer Ru complexes, based on metal cooperation. Top. Catal. 53, 915-923.
34. Sun YS, Koehler C, Tan RY, Annibale VT, Song DT (2011). Ester hydrogenation catalyzed by Ru-CNN pincer complexes. Chem. Commun. 47, 8349-8351.
35. Balaraman E, Gnanaprakasam B, Shimon LJW, Milstein D (2010). Direct hydrogenation of amides to alcohols and amines under mild conditions. J. Am. Chem. Soc. 132, 16756-16758.
36. Fogler E, Balaraman E, Ben-David Y, Leitus G, Shimon LJW, Milstein D (2011). New CNN-type ruthenium pincer NHC complexes. Mild, efficient catalytic hydrogenation of esters. Organometallics 30, 3826-3833.
37. Saudan LA, Saudan CM, Debieux C, Wyss P (2007). Dihydrogen reduction of carboxylic esters to alcohols under the catalysis of homogeneous ruthenium complexes: high efficiency and unprecedented chemoselectivity. Angew. Chem., Int. Ed. 46, 7473.
38. Saudan L, Dupau P, Riedhauser JJ, Wyss P, inventors; Firmenich SA, assignee. Hydrogenation of esters with Ru/bidentate ligands complexes. World Patent WO2006/106483. April 5, 2005.
39. Saudan L, Dupau P, Riedhauser JJ, Wyss P, inventors; Firmenich SA, assignee. Hydrogenation of esters with Ru/tetradentate ligands complexes. World Patent WO2006/106484. April 5, 2005.
40. For the preparation of complex 4, see Abdur-Rashid K, Guo RW, Lough AJ, Morris RH, Song DT (2005). Synthesis of ruthenium hydride complexes containing beta-aminophosphine ligands derived from amino acids and their use in the H2-hydrogenation of ketones and imines. Adv. Synth. Catal. 347, 571-579.
41. 3. Polyhedron 15, 1241-1251.
42. Saudan L, Saudan C, inventors; Firmenich SA, assignee. Hydrogenation of esters with Ru/bidentate ligands complexes. World Patent WO2008/065588. November 27, 2007.
43. Ino Y, Yoshida A, Kuriyama W, inventors; Takasago Int. Corp., assignee. Method for producing alcohols. European Patent EP1970360. March 10, 2008.
44. Kuriyama W, Ino Y, Ogata O, Sayo N, Saito T (2010). A homogeneous catalyst for reduction of optically active esters to the corresponding chiral alcohols without loss of optical purities. Adv. Synth. Catal. 352, 92-96
45. Ino Y, Kuriyama W, Ogata O, Matsumoto T (2010). An efficient synthesis of chiral alcohols via catalytic hydrogenation of esters. Top. Catal. 53, 1019-1024.
46. Takebayashi S, Bergens SH (2009). Facile bifunctional addition of lactones and esters at low temperatures. The first intermediates in lactone/ester hydrogenations. Organometallics 28, 2349-2351.
47. For the DKR of alpha-branched aldehydes during catalytic hydrogenation catalyzed by ruthenium complexes, see (a) Li XG, List B (2007). Catalytic asymmetric hydrogenation of aldehydes. Chem. Commun. 1739-1741.
48. Xie JH, Zhou ZT, Kong WL, Zhou QL (2007). Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: efficient synthesis of optically active primary alcohols. J. Am. Chem. Soc. 129, 1868-1869.
49. Zhou ZT, Xie JH, Zhou QL (2009). Enantioselective synthesis of chiral β-aryloxy alcohols by asymmetric hydrogenation of α-aryloxy aldehydes via dynamic kinetic resolution. Adv. Synth. Catal. 351, 363-366.
50. Narula AP (2003). The search for new fragrance ingredients. Perfumer Flavorist 62-73.
51. Mouhib H, Stahl W, Lüthy M, Büchel M, Kraft P (2011). Cassis odor through microwave eyes: olfactory properties and gas-phase structures of all the cassyrane stereoisomers and its dihydro derivatives. Angew. Chem., Int. Ed. 50, 5576-5580.
52. Olah GA, Fung AP, Malhotra R (1981). Synthetic methods and reactions; 99. Preparation of cyclic ethers over superacidic perfluorinated resinsulfonic acid (Nafion-H) catalyst. Synthesis 474-476.
53. Hunter SE, Ehrenberger CE, Savage PE (2006). Kinetics and mechanism of tetrahydrofuran synthesis via 1, 4-butanediol dehydration in high-temperature water. J. Org. Chem. 71, 6229-6239.
54. ChemSystems PERP Report Abstract PERP06/07-4 (2009).
55. Aycock DF (2007). Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions. Org. Process. Res. Dev. 11, 156-159.
56. Schniepp LE, Geller HH, Von Korff RW (1947). The preparation of acetopropyl alcohol and 1, 4-pentanediol from methylfuran. J. Am. Chem. Soc. 69, 672-674.
57. Ahmed I, inventor; Pure Energy Corp., assignee. Processes for the preparation of 2-methylfuran and 2- methyltetrahydrofuran. US Patent 2003/0018205. August 21, 2002.
58. Wabnitz T, Breuninger D, Heimann J, Backes R, Pinkos R, inventors; BASF SE, assignee. Process for one-stage preparation of 2-methyltetrahydrofuran from furfural over a catalyst. US Patent 2010/ 0099895. June 24, 2008.
59. Elliot D, Frye JG, inventors; Battelle Memorial Inst., assignee. Hydrogenated 5-carbon compound and method of making. US Patent 1999/5883266. January 16, 1998.
60. Ayoub PM, Lange JP, inventors; Shell Int. Res. Maatschappij B.V., assignee. World Patent WO2008/14127. May 21, 2008.
61. Weyer HJ, Fischer R, Merger F, Frank J, Henkelmann J, Siegel H, Ruehl T, inventors; BASF Aktiengesellschaft, assignee. Preparation of 2-methyl-1,4-butanediol and 3-methyltetrahydrofuran. US Patent 5,536,854. January 26, 1995.
62. Masaki T, Yoshikazu S, Takafumi A, inventors; Mitsubishi Gas Chem. Company Inc, assignee. Process for preparing 3-methyltetrahydrofuran. European Patent 0,773,215. November 7, 1995.
63. Ignatchenko AV, Beavers WA, Liu Z, inventors; Eastman Chem. Comp., assignee. Process for the preparation of 3-methyltetrahydrofuran. US Patent 6,521,765. April 18, 2002.
64. Manzer LE, inventor; E I Du Pont de Nemours and Co., assignee. US Patent US2003/0109724. July 9, 2002.
65. The synthesis of 2- and 3-Me-THF has also been reported by rearrangement of the corresponding vinyl oxiranes derived from isoprene and piperylene followed by hydrogenation of the dihydrofuran formed, see (a) Batory LA, McInnis CE, Njardarson JT (2006). Copper-catalyzed rearrangement of vinyl oxiranes. J. Am. Chem. Soc. 128, 16054-16055.
66. Njardarson J, Batory L, Brichacheck M, Bauer R, Rogers E, inventors; Cornell Research Foundation Inc., assignee. Production of 2,5-dihydrofurans and analogous compounds. World Patent WO2007/ 108999. March 17, 2006.
67. Geilen FMA, Engendahl B, Harwardt A, Marquardt W, Klankermayer J, Leitner W (2010). Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. Angew. Chem., Int. Ed. 49, 5510-5514.
68. Hara Y, Wada K (1991). Hydrogenation reaction of carboxylic anhydrides catalyzed by a new and highly active cationic ruthenium complex. Chem. Lett. 553-554.
69. Hara Y, Inagaki H, Nishimura S, Wada K (1992). Selective hydrogenation of cyclic ester to α, ω-diols catalyzed by cationic ruthenium complexes with trialkylphosphine ligands. Chem. Lett. 1983-1986.
70. Wylie WNO, Lough AJ, Morris RH (2010). The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(II) complex bearing a chelating N-heterocyclic carbene with a primary amine donor. Chem. Commun. 8240-8242.
71. Ikariya T, Ito M, Shibashi A, Ootsuka T, inventors; Tokyo Institute of Technology, assignee. European Patent 2,298,723. August 7, 2008.
72. Ito M, Ootsuka T, Watari R, Shiibashi A, Himizu A, Ikariya T (2011). Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand. J. Am. Chem. Soc. 133, 4240-4242.
73. 2 )Cl: imides: ( a) Ito M, Sakaguchi A, Kobayashi C, Ikariya T (2007) . Chemos elective hyd r oge nation of imides catal yz ed by Cp*Ru( PN) com plexes a nd its app li cation to the asymm etric synthesis of paroxetine. J. Am. Chem. So c. 129, 290-29 1.
74. Ito M, Kobayashi C, Himizu A, Ikariya T (2010) . Highly enantioselective hydrogenative desymmetrization of bicyclic imides leading to multipl y func ti on alized chiral cy clic compounds . J. Am. Chem. Soc. 132, 114 14- 11415.
75. N-Acylcarbamates and N-acylsulfonamides: (c) Ito M, Koo LW, Himizu A, Kobayashi C, Sakaguchi A, Ikariya T (2009). Hydrogenation of N-acylcarbamates and N-acylsulfonamides catalyzed by a bifunctional [Cp*Ru(PN)] complex. Angew. Chem., Int. Ed. 48, 1324-1327.
76. For a comprehensive compilation of Bordwell pKa data, see http://www.chem.wisc.edu/areas/ reich/pkatable/index.htm (last accessed 5 January 2012).
77. For the synthesis of substituted furans, see (a) Hou XL, Cheung HY, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HNC (1998). Regioselective syntheses of substituted furans. Tetrahedron 54, 1955-2020.
78. Keay BA (1999). Synthesis of multi-substituted furan rings: the role of silicon. Chem. Soc. Rev. 28, 209-215.
79. Ho TL, Lee KY (1995). A new synthesis of (-)-furodysin. Tetrahedron Lett. 36, 947-948.
80. Tanis SP (1982). A simple synthesis of 3-substituted furans. The preparations of dendrolasin, perillene and congeners. Tetrahedron Lett. 23, 3115-3118.
81. Tanis SP, Herrinton PM (1983). Furans in synthesis. 3. Furans as terminators in cationic cyclization. J. Org. Chem. 48, 4572-4580.
82. Marshall JA, DuBay WJ (1993). Synthesis of rosefuran. A new route to furans through basecatalyzed cyclization of hydroxy alkynoates and alkynones. J. Org. Chem. 58, 3602-3603.
83. Lipshutz BH (1986). Five-membered heteroaromatic rings as intermediates in organic synthesis. Chem. Rev. 86, 795-819.
84. Davies HML, Calvo RL, Townsend RJ, Ren PD, Churchill RM (2000). An exploratory study of type II [3+4] cycloadditions between vinylcarbenoids and dienes. J. Org. Chem. 65, 4261-4268.
85. Tanaka K, Hata T, Hara H, Katsumura S (2003). Development of new Wittig reagent, silylfuranmethylid, and its reactivity. Tetrahedron 59, 4945-4952.
86. Kuwajima I, Urabe H (1981). Regioselective synthesis of δ3-butenolides via oxidation of 2-trimethylsilylfurans. Tetrahedron Lett. 22, 5191-5194.
87. Goldsmith D, Liotta D, Saindane M, Waykole L, Bowen P (1983). 3-Alkylfurans as useful synthetic equivalents for substituted δ2-butenolides. Tetrahedron Lett. 24, 5835-5838.
88. DeShong P, Waltermire RE, Ammon HL (1988). A general approach to the stereoselective synthesis of spiroketals. A total synthesis of the pheromones of the olive fruit fly and related compounds. J. Am. Chem. Soc. 110, 1901-1910.
89. Ireland RE, Wipf P, Miltz W, Vanasse B (1990). Methodology for the enantioselective synthesis of aldols and other 1,3-dioxygenated systems. J. Org. Chem. 55, 1423-1424.
90. Cheng K, Kelly AR, Kohn RA, Dweck JF, Walsh PJ (2009). One-pot catalytic asymmetric synthesis of pyranones. Org. Lett. 11, 2703-2706.
91. Stamm S, Linden A, Heimgartner H (2003). Chiral heterospirocyclic 2H-azirin-3-amines as synthons for 3-amino-2,3,4, 5-tetrahydrofuran-3-carboxylic acid and their use in peptide synthesis. Helv. Chim. Acta 86, 1371-1396.
92. Starr D, Hixon RM (1943). Tetrahydrofuran. Org. Synth. Coll. 2, 566-568.
93. Maegawa T, Akashi A, Sajiki H (2006). A mild and facile method for complete hydrogenation of aromatic nuclei in water. Synlett 1140-1442.
94. The selective hydrogenation of heteroaromtic ketones with ruthenium complexes has been reported, see (a) Ohkuma T, Koizumi M, Yoshida M, Noyori R (2000). General asymmetric hydrogenation of hetero-aromatic ketones. Org. Lett. 2, 1749-1751.
95. Carpenter I, Clarke ML (2011). Enantioselective reduction of benzofuranyl aryl ketones. Synlett 65-68.
96. 4) (binap)(1, 2-diamine): a catalyst for asymmetric hydrogenation of simple ketones under basefree conditions. J. Am. Chem. Soc. 124, 6508-6509.
97. Kuriyama W, Ino, Y, Ogata O, inventors; Takasago Int. Corp., assignee. Alcohol production method by reducing ester or lactone with hydrogen. European Patent EP 2,161,251. September 9, 2008.
98. Grey RA, Pez GP, Wallo A, Corsi J (1980). Homogeneous catalytic hydrogenation of carboxylic acid esters to alcohols. Chem. Commun. 783-784.
99. Grey RA, Pez GP, Wallo A (1981). Anionic metal hydride catalysts. 2. Application to the hydrogenation of ketones, aldehydes, carboxylic acid esters and nitriles. J. Am. Chem. Soc. 103, 7536-7542.
100. Grey RA, Pez GP, Wallo A, Corsi J (1983). The hydrogenation of carbonyl compounds catalyzed by anionic ruthenium hydride complexes and alkali-doped supported group VIII metals. Ann. N. Y. Acad. Sci. 415, 235-243.
101. Blaser HU (2003). Enantioselective catalysis in fine chemicals production. Chem. Commun. 293-296.
102. Naud F, Spindler F, Rueggeberg CJ, Schmidt AT, Blaser HU (2007). Enantioselective ketone hydrogenation: from R&D to pilot scale with industrially viable Ru/phosphine-oxazoline complexes. Org. Process Res. Dev. 11, 519-523.